cis-(Carbonato-κ²O,O′)(rac-5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­azacyclo­tetra­decane-κ⁴N)chromium(III) bromide monohydrate

In the title compound, [Cr(CO₃)(C₁₆H₃₆N₄)]Br·H₂O, the chromium cation has a distorted octa­hedral geometry with ligation provided by the four N atoms of the `folded' macrocyclic ligand and by two O atoms of the bidentate carbonate anion. Two neighbouring chromium complexes are bridged by two strong N—H...O hydrogen bonds to form dimeric units which, in turn, are constituents of infinite chains formed by virtue of three other types of hydrogen bonds (N—H...Br, N—H...Ow and Ow—H...Br).

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.050
• wR factor = 0.117
• Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.79
PLAT432_ALERT_2_C Short Inter X...Y Contact  O3     ..  C10     ..       3.01 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.99(4), Rep   0.995(19) ......       2.11 su-Rat
              O4   -H22     1.555   1.555
PLAT748_ALERT_1_C D-H..A  Calc      173(4), Rep      173.00 ......    Missing su
              O4   -H22  -BR1     1.555   1.555   1.555

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C17 H38 Br1 Cr1 N4 O4
            Atom count from _chemical_formula_moiety:C17 H38 Cr1 N4 O4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Atwood & Barbour, 2003; Barbour, 2001); software used to prepare material for publication: X-SEED.

cis-(Carbonato-κ²O,O')(rac-5,5,7,12,12,14-hexamethyl-1,4,8,11- tetraazacyclotetradecane-κ⁴N)chromium(III) bromide monohydrate

Crystal data

[Cr(CO3)(C16H36N4)]Br·H2O	Z = 2
Mr = 494.42	F(000) = 518
Triclinic, P1	Dx = 1.511 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.633 (2) Å	Cell parameters from 2358 reflections
b = 10.924 (3) Å	θ = 2.2–24.4°
c = 13.296 (4) Å	µ = 2.39 mm^−1
α = 109.334 (4)°	T = 100 K
β = 90.305 (5)°	Prism, violet
γ = 111.828 (4)°	0.31 × 0.18 × 0.15 mm
V = 1086.5 (5) Å^3

Data collection

Bruker APEX CCD area-detector diffractometer	4995 independent reflections
Radiation source: fine-focus sealed tube	3792 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −11→11
Tmin = 0.594, Tmax = 0.695	k = −14→14
12482 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0584P)^2] where P = (Fo^2 + 2Fc^2)/3
4995 reflections	(Δ/σ)max = 0.001
252 parameters	Δρmax = 2.26 e Å^−3
3 restraints	Δρmin = −0.60 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.70364 (5)	0.28182 (4)	0.43268 (3)	0.02149 (13)
Cr1	0.24831 (6)	0.51841 (6)	0.17639 (4)	0.00890 (14)
O1	0.3043 (3)	0.4147 (2)	0.04113 (18)	0.0121 (5)
O2	0.2189 (3)	0.5843 (2)	0.05982 (18)	0.0118 (5)
O3	0.2770 (3)	0.4756 (3)	−0.10281 (18)	0.0160 (5)
O4	0.8722 (4)	0.6243 (3)	0.5356 (2)	0.0256 (6)
N1	0.2721 (3)	0.3905 (3)	0.2582 (2)	0.0122 (6)
N4	0.5068 (3)	0.6389 (3)	0.2318 (2)	0.0119 (6)
N8	0.2009 (3)	0.6703 (3)	0.3018 (2)	0.0109 (6)
N11	−0.0157 (3)	0.4028 (3)	0.1509 (2)	0.0103 (6)
C2	0.4583 (4)	0.4328 (4)	0.2802 (3)	0.0140 (7)
C3	0.5452 (4)	0.5909 (4)	0.3180 (3)	0.0135 (7)
C5	0.5810 (4)	0.7975 (4)	0.2619 (3)	0.0135 (7)
C6	0.4843 (4)	0.8644 (4)	0.3422 (3)	0.0134 (7)
C7	0.2965 (4)	0.8198 (4)	0.3088 (3)	0.0118 (7)
C9	0.0159 (4)	0.6281 (4)	0.2851 (3)	0.0141 (7)
C10	−0.0709 (4)	0.4703 (4)	0.2533 (3)	0.0127 (7)
C12	−0.0909 (4)	0.2426 (4)	0.1119 (3)	0.0129 (7)
C13	−0.0101 (4)	0.1927 (4)	0.1850 (3)	0.0147 (7)
C14	0.1810 (4)	0.2352 (4)	0.1978 (3)	0.0135 (7)
C15	0.7667 (4)	0.8616 (4)	0.3121 (3)	0.0176 (8)
C16	0.5746 (5)	0.8283 (4)	0.1579 (3)	0.0175 (8)
C17	0.2346 (4)	0.9224 (4)	0.3902 (3)	0.0154 (8)
C18	−0.2816 (4)	0.1876 (4)	0.1131 (3)	0.0177 (8)
C19	−0.0609 (5)	0.1862 (4)	−0.0048 (3)	0.0166 (8)
C20	0.2250 (5)	0.1489 (4)	0.2557 (3)	0.0195 (8)
C21	0.2690 (4)	0.4912 (4)	−0.0070 (3)	0.0126 (7)
H1	0.2318	0.4140	0.3235	0.015*
H2A	0.4994	0.3895	0.2138	0.017*
H2B	0.4841	0.3990	0.3362	0.017*
H3A	0.5052	0.6344	0.3848	0.016*
H3B	0.6686	0.6202	0.3338	0.016*
H4	0.5613	0.6054	0.1756	0.014*
H6A	0.4974	0.8447	0.4086	0.016*
H6B	0.5396	0.9681	0.3614	0.016*
H7	0.2797	0.8252	0.2362	0.014*
H8	0.2302	0.6633	0.3664	0.013*
H9A	−0.0203	0.6754	0.3524	0.017*
H9B	−0.0154	0.6575	0.2278	0.017*
H10A	−0.1948	0.4410	0.2428	0.015*
H10B	−0.0407	0.4407	0.3107	0.015*
H11	−0.0588	0.4259	0.0988	0.012*
H13A	−0.0404	0.2269	0.2578	0.018*
H13B	−0.0639	0.0882	0.1580	0.018*
H14	0.2157	0.2117	0.1246	0.016*
H15A	0.7754	0.8421	0.3782	0.026*
H15B	0.8306	0.8198	0.2609	0.026*
H15C	0.8129	0.9640	0.3292	0.026*
H16A	0.6375	0.7836	0.1080	0.026*
H16B	0.6253	0.9306	0.1747	0.026*
H16C	0.4570	0.7903	0.1245	0.026*
H17A	0.2978	1.0185	0.3916	0.023*
H17B	0.1142	0.8949	0.3687	0.023*
H17C	0.2525	0.9194	0.4620	0.023*
H18A	−0.3042	0.2239	0.1869	0.027*
H18B	−0.3333	0.2197	0.0666	0.027*
H18C	−0.3293	0.0841	0.0865	0.027*
H19A	−0.1134	0.2201	−0.0494	0.025*
H19B	−0.1107	0.0827	−0.0321	0.025*
H19C	0.0606	0.2197	−0.0077	0.025*
H20A	0.1886	0.1688	0.3269	0.029*
H20B	0.1673	0.0480	0.2131	0.029*
H20C	0.3472	0.1750	0.2639	0.029*
H22	0.829 (6)	0.520 (2)	0.501 (5)	0.10 (2)*
H23	0.992 (2)	0.662 (4)	0.553 (4)	0.058 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0215 (2)	0.0253 (2)	0.0176 (2)	0.00562 (17)	0.00318 (15)	0.01172 (17)
Cr1	0.0091 (3)	0.0095 (3)	0.0086 (3)	0.0039 (2)	0.0024 (2)	0.0036 (2)
O1	0.0142 (13)	0.0151 (13)	0.0103 (12)	0.0089 (10)	0.0045 (10)	0.0049 (10)
O2	0.0120 (12)	0.0145 (13)	0.0113 (12)	0.0070 (10)	0.0027 (9)	0.0055 (10)
O3	0.0178 (13)	0.0219 (14)	0.0092 (12)	0.0092 (11)	0.0024 (10)	0.0053 (11)
O4	0.0249 (16)	0.0289 (18)	0.0212 (15)	0.0114 (13)	0.0057 (12)	0.0060 (13)
N1	0.0100 (15)	0.0149 (16)	0.0127 (15)	0.0055 (12)	0.0024 (11)	0.0058 (12)
N4	0.0107 (15)	0.0127 (15)	0.0130 (14)	0.0048 (12)	0.0045 (11)	0.0051 (12)
N8	0.0101 (14)	0.0139 (15)	0.0104 (14)	0.0053 (12)	0.0019 (11)	0.0060 (12)
N11	0.0101 (14)	0.0101 (15)	0.0101 (14)	0.0032 (12)	0.0013 (11)	0.0040 (12)
C2	0.0097 (17)	0.0191 (19)	0.0140 (17)	0.0065 (15)	0.0010 (13)	0.0062 (15)
C3	0.0106 (17)	0.0183 (19)	0.0144 (18)	0.0082 (15)	0.0031 (14)	0.0061 (15)
C5	0.0116 (17)	0.0128 (18)	0.0156 (18)	0.0036 (14)	0.0032 (14)	0.0060 (15)
C6	0.0140 (18)	0.0095 (18)	0.0155 (18)	0.0050 (14)	0.0021 (14)	0.0027 (14)
C7	0.0115 (17)	0.0096 (17)	0.0140 (17)	0.0031 (14)	0.0026 (14)	0.0051 (14)
C9	0.0115 (17)	0.0170 (19)	0.0125 (17)	0.0062 (15)	0.0020 (13)	0.0032 (15)
C10	0.0122 (17)	0.0148 (19)	0.0101 (17)	0.0049 (15)	0.0031 (13)	0.0035 (14)
C12	0.0137 (18)	0.0097 (18)	0.0126 (17)	0.0014 (14)	0.0003 (14)	0.0043 (14)
C13	0.0161 (19)	0.0125 (19)	0.0163 (18)	0.0054 (15)	0.0029 (14)	0.0063 (15)
C14	0.0136 (18)	0.0119 (18)	0.0158 (18)	0.0049 (15)	0.0055 (14)	0.0059 (15)
C15	0.0124 (18)	0.015 (2)	0.0209 (19)	0.0043 (15)	0.0017 (15)	0.0031 (16)
C16	0.0178 (19)	0.018 (2)	0.0189 (19)	0.0056 (16)	0.0072 (15)	0.0102 (16)
C17	0.0102 (17)	0.0139 (19)	0.0205 (19)	0.0061 (15)	0.0002 (14)	0.0026 (15)
C18	0.0105 (18)	0.021 (2)	0.023 (2)	0.0046 (15)	0.0025 (15)	0.0105 (17)
C19	0.021 (2)	0.0124 (19)	0.0125 (18)	0.0051 (16)	0.0022 (15)	0.0020 (15)
C20	0.024 (2)	0.016 (2)	0.022 (2)	0.0099 (17)	0.0024 (16)	0.0082 (16)
C21	0.0066 (16)	0.0131 (18)	0.0139 (18)	0.0006 (14)	0.0012 (13)	0.0035 (14)

Geometric parameters (Å, º)

Cr1—O1	1.954 (2)	C14—C20	1.539 (5)
Cr1—O2	1.964 (2)	C14—H14	1.0000
Cr1—N8	2.093 (3)	C3—H3A	0.9900
Cr1—N1	2.096 (3)	C3—H3B	0.9900
Cr1—N4	2.100 (3)	C9—C10	1.505 (5)
Cr1—N11	2.115 (3)	C9—H9B	0.9900
O1—C21	1.319 (4)	C9—H9A	0.9900
O3—C21	1.234 (4)	C19—H19A	0.9800
N8—C9	1.481 (4)	C19—H19B	0.9800
N8—C7	1.500 (4)	C19—H19C	0.9800
N8—H8	0.9300	C10—H10B	0.9900
O4—H22	0.995 (19)	C10—H10A	0.9900
O4—H23	0.953 (19)	C18—H18B	0.9800
N1—C2	1.495 (4)	C18—H18A	0.9800
N1—C14	1.496 (4)	C18—H18C	0.9800
N1—H1	0.9300	C20—H20C	0.9800
O2—C21	1.321 (4)	C20—H20B	0.9800
N11—C10	1.492 (4)	C20—H20A	0.9800
N11—C12	1.518 (4)	C13—H13A	0.9900
N11—H11	0.9300	C13—H13B	0.9900
N4—C3	1.491 (4)	C7—C6	1.525 (5)
N4—C5	1.511 (4)	C7—H7	1.0000
N4—H4	0.9300	C5—C6	1.523 (5)
C17—C7	1.537 (5)	C5—C16	1.532 (5)
C17—H17B	0.9800	C5—C15	1.533 (5)
C17—H17A	0.9800	C6—H6B	0.9900
C17—H17C	0.9800	C6—H6A	0.9900
C2—C3	1.502 (5)	C15—H15B	0.9800
C2—H2A	0.9900	C15—H15A	0.9800
C2—H2B	0.9900	C15—H15C	0.9800
C12—C18	1.530 (5)	C16—H16A	0.9800
C12—C19	1.531 (5)	C16—H16B	0.9800
C12—C13	1.536 (5)	C16—H16C	0.9800
C14—C13	1.530 (5)
O1—Cr1—O2	67.59 (10)	C2—C3—H3A	109.9
O1—Cr1—N8	164.48 (10)	N4—C3—H3B	109.9
O2—Cr1—N8	97.91 (10)	C2—C3—H3B	109.9
O1—Cr1—N1	95.06 (11)	H3A—C3—H3B	108.3
O2—Cr1—N1	161.49 (11)	N8—C9—C10	109.3 (3)
N8—Cr1—N1	99.92 (11)	N8—C9—H9B	109.8
O1—Cr1—N4	89.37 (11)	C10—C9—H9B	109.8
O2—Cr1—N4	99.97 (10)	N8—C9—H9A	109.8
N8—Cr1—N4	87.74 (11)	C10—C9—H9A	109.8
N1—Cr1—N4	85.68 (11)	H9B—C9—H9A	108.3
O1—Cr1—N11	99.68 (10)	C12—C19—H19A	109.5
O2—Cr1—N11	88.64 (10)	C12—C19—H19B	109.5
N8—Cr1—N11	84.96 (11)	H19A—C19—H19B	109.5
N1—Cr1—N11	88.03 (11)	C12—C19—H19C	109.5
N4—Cr1—N11	169.41 (11)	H19A—C19—H19C	109.5
C21—O1—Cr1	90.80 (19)	H19B—C19—H19C	109.5
C9—N8—C7	112.3 (3)	N11—C10—C9	108.3 (3)
C9—N8—Cr1	105.4 (2)	N11—C10—H10B	110.0
C7—N8—Cr1	114.6 (2)	C9—C10—H10B	110.0
C9—N8—H8	108.1	N11—C10—H10A	110.0
C7—N8—H8	108.1	C9—C10—H10A	110.0
Cr1—N8—H8	108.1	H10B—C10—H10A	108.4
H22—O4—H23	109 (3)	C12—C18—H18B	109.5
C2—N1—C14	112.0 (3)	C12—C18—H18A	109.5
C2—N1—Cr1	104.1 (2)	H18B—C18—H18A	109.5
C14—N1—Cr1	114.5 (2)	C12—C18—H18C	109.5
C2—N1—H1	108.7	H18B—C18—H18C	109.5
C14—N1—H1	108.7	H18A—C18—H18C	109.5
Cr1—N1—H1	108.7	C14—C20—H20C	109.5
C21—O2—Cr1	90.33 (19)	C14—C20—H20B	109.5
C10—N11—C12	113.5 (3)	H20C—C20—H20B	109.5
C10—N11—Cr1	104.00 (19)	C14—C20—H20A	109.5
C12—N11—Cr1	121.1 (2)	H20C—C20—H20A	109.5
C10—N11—H11	105.7	H20B—C20—H20A	109.5
C12—N11—H11	105.7	C14—C13—C12	119.3 (3)
Cr1—N11—H11	105.7	C14—C13—H13A	107.5
C3—N4—C5	114.1 (3)	C12—C13—H13A	107.5
C3—N4—Cr1	104.4 (2)	C14—C13—H13B	107.5
C5—N4—Cr1	121.3 (2)	C12—C13—H13B	107.5
C3—N4—H4	105.2	H13A—C13—H13B	107.0
C5—N4—H4	105.2	N8—C7—C6	110.1 (3)
Cr1—N4—H4	105.2	N8—C7—C17	111.6 (3)
O3—C21—O1	124.7 (3)	C6—C7—C17	109.1 (3)
O3—C21—O2	124.0 (3)	N8—C7—H7	108.7
O1—C21—O2	111.3 (3)	C6—C7—H7	108.7
C7—C17—H17B	109.5	C17—C7—H7	108.7
C7—C17—H17A	109.5	N4—C5—C6	110.6 (3)
H17B—C17—H17A	109.5	N4—C5—C16	107.7 (3)
C7—C17—H17C	109.5	C6—C5—C16	111.5 (3)
H17B—C17—H17C	109.5	N4—C5—C15	110.9 (3)
H17A—C17—H17C	109.5	C6—C5—C15	108.6 (3)
N1—C2—C3	109.3 (3)	C16—C5—C15	107.4 (3)
N1—C2—H2A	109.8	C5—C6—C7	118.2 (3)
C3—C2—H2A	109.8	C5—C6—H6B	107.7
N1—C2—H2B	109.8	C7—C6—H6B	107.7
C3—C2—H2B	109.8	C5—C6—H6A	107.7
H2A—C2—H2B	108.3	C7—C6—H6A	107.7
N11—C12—C18	110.1 (3)	H6B—C6—H6A	107.1
N11—C12—C19	108.2 (3)	C5—C15—H15B	109.5
C18—C12—C19	107.9 (3)	C5—C15—H15A	109.5
N11—C12—C13	109.9 (3)	H15B—C15—H15A	109.5
C18—C12—C13	109.4 (3)	C5—C15—H15C	109.5
C19—C12—C13	111.4 (3)	H15B—C15—H15C	109.5
N1—C14—C13	111.0 (3)	H15A—C15—H15C	109.5
N1—C14—C20	111.2 (3)	C5—C16—H16A	109.5
C13—C14—C20	108.8 (3)	C5—C16—H16B	109.5
N1—C14—H14	108.6	H16A—C16—H16B	109.5
C13—C14—H14	108.6	C5—C16—H16C	109.5
C20—C14—H14	108.6	H16A—C16—H16C	109.5
N4—C3—C2	108.8 (3)	H16B—C16—H16C	109.5
N4—C3—H3A	109.9
O2—Cr1—O1—C21	0.43 (18)	N8—Cr1—N4—C5	−45.2 (2)
N8—Cr1—O1—C21	−21.4 (5)	N1—Cr1—N4—C5	−145.4 (2)
N1—Cr1—O1—C21	173.76 (19)	N11—Cr1—N4—C5	−91.6 (6)
N4—Cr1—O1—C21	−100.63 (19)	Cr1—O1—C21—O3	−178.7 (3)
N11—Cr1—O1—C21	84.9 (2)	Cr1—O1—C21—O2	−0.6 (3)
O1—Cr1—N8—C9	95.5 (4)	Cr1—O2—C21—O3	178.8 (3)
O2—Cr1—N8—C9	75.2 (2)	Cr1—O2—C21—O1	0.6 (3)
N1—Cr1—N8—C9	−99.9 (2)	C14—N1—C2—C3	167.5 (3)
N4—Cr1—N8—C9	174.9 (2)	Cr1—N1—C2—C3	43.2 (3)
N11—Cr1—N8—C9	−12.7 (2)	C10—N11—C12—C18	48.7 (4)
O1—Cr1—N8—C7	−28.6 (5)	Cr1—N11—C12—C18	173.4 (2)
O2—Cr1—N8—C7	−48.9 (2)	C10—N11—C12—C19	166.4 (3)
N1—Cr1—N8—C7	136.1 (2)	Cr1—N11—C12—C19	−68.9 (3)
N4—Cr1—N8—C7	50.9 (2)	C10—N11—C12—C13	−71.8 (3)
N11—Cr1—N8—C7	−136.8 (2)	Cr1—N11—C12—C13	52.9 (3)
O1—Cr1—N1—C2	73.9 (2)	C2—N1—C14—C13	175.0 (3)
O2—Cr1—N1—C2	93.7 (4)	Cr1—N1—C14—C13	−66.8 (3)
N8—Cr1—N1—C2	−102.0 (2)	C2—N1—C14—C20	53.7 (4)
N4—Cr1—N1—C2	−15.1 (2)	Cr1—N1—C14—C20	171.9 (2)
N11—Cr1—N1—C2	173.5 (2)	C5—N4—C3—C2	177.4 (3)
O1—Cr1—N1—C14	−48.7 (2)	Cr1—N4—C3—C2	42.8 (3)
O2—Cr1—N1—C14	−29.0 (4)	N1—C2—C3—N4	−60.4 (3)
N8—Cr1—N1—C14	135.3 (2)	C7—N8—C9—C10	167.0 (3)
N4—Cr1—N1—C14	−137.7 (2)	Cr1—N8—C9—C10	41.5 (3)
N11—Cr1—N1—C14	50.8 (2)	C12—N11—C10—C9	178.3 (3)
O1—Cr1—O2—C21	−0.43 (18)	Cr1—N11—C10—C9	44.8 (3)
N8—Cr1—O2—C21	173.80 (19)	N8—C9—C10—N11	−60.4 (3)
N1—Cr1—O2—C21	−21.8 (4)	N1—C14—C13—C12	68.5 (4)
N4—Cr1—O2—C21	84.7 (2)	C20—C14—C13—C12	−168.8 (3)
N11—Cr1—O2—C21	−101.48 (19)	N11—C12—C13—C14	−58.7 (4)
O1—Cr1—N11—C10	177.48 (19)	C18—C12—C13—C14	−179.6 (3)
O2—Cr1—N11—C10	−115.5 (2)	C19—C12—C13—C14	61.3 (4)
N8—Cr1—N11—C10	−17.5 (2)	C9—N8—C7—C6	171.7 (3)
N1—Cr1—N11—C10	82.7 (2)	Cr1—N8—C7—C6	−68.0 (3)
N4—Cr1—N11—C10	29.1 (7)	C9—N8—C7—C17	50.5 (4)
O1—Cr1—N11—C12	48.5 (2)	Cr1—N8—C7—C17	170.8 (2)
O2—Cr1—N11—C12	115.5 (2)	C3—N4—C5—C6	−73.5 (3)
N8—Cr1—N11—C12	−146.4 (2)	Cr1—N4—C5—C6	52.7 (3)
N1—Cr1—N11—C12	−46.3 (2)	C3—N4—C5—C16	164.3 (3)
N4—Cr1—N11—C12	−99.9 (6)	Cr1—N4—C5—C16	−69.4 (3)
O1—Cr1—N4—C3	−110.0 (2)	C3—N4—C5—C15	47.1 (4)
O2—Cr1—N4—C3	−177.1 (2)	Cr1—N4—C5—C15	173.3 (2)
N8—Cr1—N4—C3	85.3 (2)	N4—C5—C6—C7	−59.6 (4)
N1—Cr1—N4—C3	−14.9 (2)	C16—C5—C6—C7	60.2 (4)
N11—Cr1—N4—C3	38.9 (7)	C15—C5—C6—C7	178.4 (3)
O1—Cr1—N4—C5	119.5 (2)	N8—C7—C6—C5	69.8 (4)
O2—Cr1—N4—C5	52.4 (2)	C17—C7—C6—C5	−167.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···Br1^i	0.93	2.55	3.441 (3)	161
N1—H1···O4^i	0.93	2.18	3.045 (4)	155
N11—H11···O2^ii	0.93	2.46	3.368 (4)	164
N11—H11···O3^ii	0.93	2.49	3.168 (4)	130
N4—H4···O3^iii	0.93	2.01	2.888 (4)	157
O4—H22···Br1	0.99 (4)	2.26 (4)	3.245 (3)	173
O4—H23···Br1^iv	0.95 (3)	2.46 (2)	3.398 (4)	169

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z; (iv) −x+2, −y+1, −z+1.